Key West Sailing Trips

Key West Sailing Trips

Cruises, Sailing & Water Tours See all

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Champagne Celebration Sunset Cruise

5 star rating: Highly Recommended 36 Reviews

Get out on Key West’s beautiful Atlantic waters to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are Chandon Brut ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $73.99

Tall Ship Sunset Cruise in Key West

5 star rating: Highly Recommended 4 Reviews

Enjoy an exquisite 2-hour sunset sailing adventure in Key West aboard a stunning tall ship! Take in great views of Mallory Square, Sunset Pier, Sand Key Light ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $74.99

Key West Schooner Sailing

5 star rating: Highly Recommended 4 Reviews

Take to the sea aboard an 1890s-style schooner from Key West and admire its beauty on the clear, calm Caribbean waters! As you sail through the turquoise ...  Read more

Location: Key West, Florida
Duration: 1 hour 30 minutes (approx.)

From USD $44.99

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 18 Reviews

Spend a beautiful Florida day out in the clear, blue waters off Key West. On the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise, you’ll spot ...  Read more

Location: Key West, Florida
Duration: 4 hours (approx.)

From USD $95.59

Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips

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